


Right Up There

by orphan_account



Category: Original Work
Language: English
Status: Completed
Published: 2018-06-09
Updated: 2018-06-09
Packaged: 2019-05-20 05:18:37
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 6,495
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14888369
Author URL: https://archiveofourown.org/users/orphan_account/pseuds/orphan_account





	Right Up There

He nervously awaits her arrival. It's been nearly a week since he somewhat drunkenly confessed to his best friend that he'd been... dabbling in crossdressing, after she told him that a mutual acquaintence of theirs had gotten back into touch with her, and that she was a makeup artist who specializes in crossdressers... and that she, herself, had a penis. He hadn't meant to blurt out that he was, himself, a crossdresser, but after he sobered up he realized that, likely, she hadn't been telling him that idly. The way she talked her up after he expressed interest... oh, she's gorgeous, and oh, she's so sweet, and oh, she'll be able to make you so pretty... she's older and mature, but playful, and she loves dressing up blondes... made him think that he'd signed up for more of a blind date than a makeover date... but he wasn't about to pass up the opportunity, regardless. His friend, Taylor, told him to make himself and his one-room look presentable next Saturday at noon, and he agreed - unlikely as it was that he'd have agreed sober, he didn't regret agreeing, either. What he did regret was not asking her what "presentable" meant - en femme, or en homme? So he'd somewhat split the difference, wearing his hair down, a neutral-gendered button down with only slightly frilly sleeves, a pair of slacks, kitten heels, and just a hint of make-up (which only took him half an hour to put on), including some eye liner and the idea of mascara more than the physical stuff. Having finally moved out on his own, he no longer needed to steal his mom or his sister's skirts - he could buy his own... but he'd only bought a handful.

Once dressed, he had sat on one of the two chairs he kept for entertaining guests... and waited.

It's almost two o' clock now, and no sign of her. He starts to fidget in his seat - the longer he wears his weak-game make-up, the worse it will look. And, of course, he worries that she won't show at all, after all. 

There's a knock on the door, and he jumps out of his seat, but then frezes in place. It had been quiet enough that he might have missed it, but his nerves are so attuned to his surroundings that any disturbance at all would have been like a wrecking ball taking out his wall.

He looks through the peephole - and is surprised to see a very normal looking girl waiting. Her make-up was barely noticable - but then, perhaps that's the point. She is rather busty, and her hair does look like it took a lot of effort to make it look that effortless, but he had been expecting her to be more ostentatious, for some reason. 

He opens the door, and then sheepishly says "come in," then steps aside to let her pass. As she does, he catches her fragrance... engine grease. She's rolling a suitcase behind her - does she really have that much make-up?

"Sorry 'bout the wait; car broke down," she says, and she certainly does have a full, matronly voice with a pronounced twang. He had also been expecting her to be more... urban.

"Oh, no, hey, that's fine. Did you have to have it towed, or...?"

"Just fixed it myself. I'm good with my hands, as you can imagine," she says, and he looks at her quixotically, until she pantomimes putting on blush, and nods in delayed understanding.

"That's good to hear. Do you want to sit down...?" he asks, gesturing to the chair and the small wooden fold-out table between them. She contemplates it for a moment, then looks back to him.

"Taylor told me about you. She said you're looking for some help."

"Y-yeah. She said we should hoo-- meet up. I think we've met before."

"I think I'd remember if I met a cute boy like you," she says, and he suddenly doesn't know what to do with his hands. "I'm Charlene. And I know who you are... but... what should I call you?"

"C...Cydney."

"Pretty name for a pretty girl. So, Cydney, what do you need from me?" she asks, staring right through "Cydney", who can barely stand the attention.

"I... I want to crossdress."

"Well, that's interesting... I'd like to see that," she says, and he swallows with an audible gulp. 

"I-I've been doing it for a while... and... I don't really know how to do it... and I just thought... you'd be a good person to ask."

"Why, because I know how to tuck? Or because I know what dress looks best with a big ol' cock?" she says, then giggles. 

He winces. "I... I didn't mean anything by it."

"I'm just messin' with ya. Just curious what kind of thoughts are rollin' around in that pretty little blonde head of yours."

Cydney is stunned. He wasn't expecting that.

"Am I... pretty?"

She smirks. "Well, you're certainly a cutey, with those big blue eyes and that strawberry hair. And, mmm... I wouldn't say you're not pretty, but... there's a whole world of pretty, and you just stepped out the wardrobe. Speaking of wardrobes, that's where we'll start."

"So you'll help me?"

She looks him up and down. "Sure, I can help pretty you up... but it's going to cost you."

"That's fine, how much are we talkin'?"

"I wasn't thinkin' of being paid in dollars, honey. How are you with a cock?"

He can't look at her in the eye, and it's obvious that she wants him to. He looks all around the room, feeling a little damp.

"I... wouldn't know."

"Mmmm... that's interesting. Never handled your own?"

"Well, I have but... I've only been with..." he says, trying to find the words. 

She raises an eyebrow. "Have you now?"

"S-sure."

"How many?"

"Tw... three."

"Two or three? Or did one not count?"

"I mean... I say 'been with', but..."

Her face lights up, and her mouth opens wide, before narrowing into a set of plump, beglossed pursed lips. "You're a virgin, ain'tcha."

"...yeah."

"Ain't no shame in that," she says. "But there is shame in lyin' to a lady. By two or three, you meant a big fat nothin', didn't you?"

"Yeah... I'm sorry. I wasn't trying to lie..."

"I'm just teasin'. So. Should we negotiate? Or do you just want me to pretty you up, and we'll settle the details later?" she asks, and he nods, late enough that she knows he wants to get to it.

"First, we'll do your hair and your face. Then... we'll do the rest of you," she says, and he feels a little twinge in the pit of his stomach. His living space doesn't have much, but it does have a big mirror, and she directs him to move his chair in front of it. While he does that, she opens up her bag to reveal not only make-up products, but clothing of various types - all women's, though. "Alright - first we'll clip your hair out of your face. Any preferences? Do you want to look like a movie star? Like a home-grown gal? Spunky and punky?" she says, pulling his hair out of the way.

"I guess... whatever you want is fine."

"Whatever I want, huh? Well, that makes it easy," she says while clipping his hair, then she starts to remove the make-up he had already put on. "Go easy with the contouring... you've already got a strongly defined face... and you don't need this much blush... well, not now at least," she teases, and he has to look back up from her cleavage to her face just in time to see her stick out her tongue. Once she's done with the make-up removal, she goes to work, occasionally telling him to turn his head, or flutter his eyelashes, and, eventually, she unclips his hair, and pulls two pink ribbons from her bag. "Take off your blouse," she says, and he hesitantly obeys, unbuttoning each button before worming out of it and handing it to her, but she just discards it on the floor. She pulls a magenta shirt on over his head... and it leaves his entire midriff exposed. Then ties up his hair in shoulder length, unbraided pigtails, finishing each off with a bow.

He looks at himself in the mirror both over and underwhelmed - whelmed in two directions. On the one hand, he didn't look that different from his usual self. On the other hand, he looked totally different from his usual self. He could easily pass for a girl... someone who knew him expecting to see him would be able to tell that it was him right away, but someone who didn't... he felt himself getting a little... excited, and squirmed in his seat.

"Here, stand up. Tell me what you think," she says, and he does, although he has difficulty doing so without exposing his arousal. "Oh, it looks pretty good... but those pants have got to git."

"Should I... take them off?" he asks, looking back at her for confirmation. She bites her nail.

"Do whatever you want, honey. But I think you should."

He nods, and unzips them in the back, feeling more than a little self-conscious. He draws them down over his hips and ass, then down to the floor, and then kicks them off his feet - and she whistles, seeing him standing there in a pair of panties, kitten heels, and a belly-baring barbie-pink sleeveless top.

"Wow. Talk about lucky. If you want to pass, you just have to face away from someone and bend over to pick something up," she says, looking him up and down. While that teasing makes him red in the ears, he's glad that she is facing his backside, because otherwise there'd be no hiding it. "Hey... what are you smuggling in those panties?" she asks, and just then, he remembers the mirror. 

"Um... sorry."

"No need to be sorry. But those panties have got to go. They don't match," she says, and he hooks his fingers to pull them down, and takes a deep breath. 

"Do you have new ones?"

"Yeah, I've got plenty," she says, and he nods... and looks down at himself as he drops his panties to the floor. He hears her heels clicking on the floor behind him, and then her finger runs down the small of his back, giving him chills.

"Shouldn't I put on some... pants, or something?" he asks, looking over his shoulder at her face.

"You don't need pants to look pretty. For instance, I'm not wearing any."

"You're... naked?"

"No, I just took off my pants. Can't you tell?"

He can. Something is poking between his thighs.

"Hey... wanna have sex?" she says, bluntly. "Or do you crossdress just for fun?"

"Charlene, I'm... I..." he says, squirming, as she runs her finger up and down his back, up to the nape of his neck, down to his tailbone. 

"You're looking for love? Is that what you want to say? Cydney?"

He couldn't even convincingly lie at this point - she can see in the mirror how excited she's making him.

"H-how... do you want to..." he asks, sheepishly, knowing the answer deep down, and knowing that the answer is "deep down".

"Well, if we're both facing the mirror like this... our options are kinda limited," she says, bringing herself closer to him, bringing a hand around to his front, to the region just above his unseemly thing.

"I... I could turn around," he says, enjoying the feeling of her hand as it runs along his abdomen, or her other hand, as it feels cool to the touch on his hot, bare cheek.

"Yeah... but you won't," she says, all but confirming that she intends to go spelunking in his boy cave. "For a boy, you sure got a nice fat ass... I'm a little jealous."

"Hnn..." is all he can reply as she swats his rear playfully, then grabs a handful and shakes it. 

"You like being touched there, don't you? Tell me... do you like cross-dressing... or do you like being treated like a girl?"

"I... I do..."

"You like being treated like a girl... sexually?" she asks, but she doesn't wait for an answer as she leans in to kiss the nape of his neck, then whispers in his ear. "You want to be fucked?"

He moans softly, feeling her thing resting between his thighs, as she paws at his ass, and her other hand explores his chest and tummy. "D-do you... do you have... something... to..."

"You mean do I have plenty of lube on me for anal sex? Sure do. No use beatin' around the bush, honey, unless that's what you're into - both of us want to fuck, and I wouldn't place any bets on who wants to fuck more," she says, squatting down to reach her bag. While she's down there, she runs her hands down his inner thighs... then spreads his cheeks and gives him a kiss, right on the money. "Mmm... I don't give tongue on the first date, unfortunately," she says, while she rummages for supplies. When she finds it, he hears a cap pop open. "Bend over, stick out that big ol' ass o' yours, spread your cheeks, and I'll grease up that shitter so good you'll feel like the belle of the ball on her fourth helpin'."

He bends over, steadying himself on the mirror, at first, then reaches back to pull his cheeks apart. As soon as he does, she's there, applying lubricant a lot more liberally than she applied the make-up.

"Are you... really gonna fuck me?" he asks as she lubes up his asshole, first with a finger on the outside, then the inside, then two fingers on the inside. She doesn't answer until the two fingers have thoroughly demonstrated how silly a question that is.

"I am really gonna fuck you, honey. Right up the ass. How ya feelin'? Excited? Nervous? Horny as all get out? Or all of the above."

"All of that, and a little embarassed..." he admits, as she thwats her dong on his big ripe pear.

"It'll start to be clearer once I stick ya. You ready for your anal debut, hon?"

"I think so... just don-- hnk!"

He was cut off by a sudden intrusion into his backdoor - the flared head of her penis, popping in with (relative) ease.

"Don't do what? Hon? I hope you weren't about to say pop my love rocket in your cock socket, cuz that ship is sailin'."

"Oh... fuck..." he says, feeling it stretch his O-ring open. Whatever he was going to say, he forgot it.

With one hand feeding it in, and the other on his shoulder, she remains motionless for a turn. "Just let me know when you're ready for more, darlin'. Not hungry for more, cuz I know that's right now, just ready."

With a deep breath, he calms himself down. He nods, and she starts to feed more up into him at a glacial pace - and glacier is right, because an inevitable mass that crushes everything in its path was an apt description of her meat.

"Ooh, that is tight. I guess you weren't lying about bein' a virgin. I am really going to have to work to get all up in that poo-say. Hey, how are you doin' up top? Still a virgin?" 

"...fuck...!"

"I'll take that as a yes. Ever done anything with your cock?"

"No... fuck... hold on..."

"Holding on, but I think I just heard you admit you're an ass-first kinda guy. Well, I'll have to give it you nice and thorough so you know for sure this is the night you lost it. A lot less ambiguity about the whole thing if you wake up tomorrow feeling like you got fucked by a train."

"No, go easy..."

"Oh, I'll start easy. I'm gonna work up to it. Well, first, I've got to work up it. Up it goes," she says, feeding more and more of it up and in. With the aide of the lube, his hole wasn't being too irritated, but it was starting to spasm, and his stomach was tying itself into knots at the strange intrusion from the wrong direction.

It dawns on him that he's having sex for the first time, and no one has ever touched his cock. As it slides deeper and deeper inside, he feels less and less like this won't count as his first time, and more and more like there's a big dick in his ass.

Eventually, she releases her own, letting it stick in by itself, and when she's satisfied it won't slip out, she wraps both hands around his hips.

"Now I've got it good and jammed in there. Look ma, no hands... can you push me out?"

"Nnh... no," he groans, after trying.

"Yeah, but I like to feel ya try it. Now I can use both my hands... isn't that nice," she says, running her hands up and down his waist, hips, and thighs, while her cockhead kisses open the smooth muscle in his rectum.

His whole body feels sensitive to her touch, and he's dribbling all over the floor. Looking at their reflections in the mirror, it looks like she's just embracing him from behind, but the truth is much, much deeper, if not balls-deep. Looking like he does, feeling like he does, he has little doubt that he's going to have any regrets, but feeling her sink depeer and deeper into his irritated guts, he worries that his body might not agree. 

She takes a step forward, gashunking about half an inch of cock shaft into his ass, making him sputter. Then, using her newfound closeness, she rests her chin on his collarbone.

"There, now I can see your face as you cum. Well, lookit'chu. The prettiest belle with blocked-up bowels I ever did see. I can see it on your face - you're holdin' back. If I look down, am I gonna see a limp noodle?"

He shakes his head.

"How stiff is it? So stiff it hurts? Stiffer than mine? Whose stiffer - me or you?"

"You feel so hard..."

"I AM so hard, honey. It may feel harder because it's all up in your squishy guts, poking around and wrecking the place, but it is hard as a rock. It's hard for you, honey. Is yours hard for me?"

"So hard..."

"How did I make you so hard?"

"By putting it up my ass..."

"That all it took? Not my pretty looks and my flirtin' - just one straight up the dirty hole? I'm startin' to think you didn't invite me here for my make-up skills. Then again, you're just now learnin' about my puttin'-it-to-a-boy skills. How's my anal sex, honey?"

"It's... nnh..."

"Feel that pressure building? It's going in... I'm taking your virginity. I'm cramming it right up there. Awww... you're blushing. Do you love it? Don't worry... I'll take care of you, blondie... I'll go slow... then, I'll make you think your name really is Cydney!" 

He feels her starting to sink in faster... his hungry hole gobbling her up as fast as it can. He groans as she bottosm out more and more, until, finally, with a soft, inaudible tap, her hips hit against his soft, cushioned rear, and Charlene had bottomed out inside "Cydney".

"Hey," she says, and lets the word linger in the air as he shudders and sighs. "Did you notice? We're together now. I ran outta cock... but you ain't run outta ass. Guess that means we're compatible," she says, kissing his neck... then giving him a little lick on the cheek. "Well, I guess I should wait to see if your thing fits snugly in me... but I think this is the way we both want it, anyway."

The full length of her dick inside him, it felt like it was longer than his - although, he was sure anything felt longer when it was lodged where her thing was lodged. He could feel her veins, he could feel the shape of her head, he definitely feel something hard and metal on the underside which seemed like something only advanced cock-holsters should attempt... most importantly, he felt her pulsing. Not only that, her balls were on his thighs, fat and happy, obviously in a fuller state than they would have been if they didn't think she was in a prime mating scenario. He never thought his fat rear would convince a pair of eggs that it was time to pump out sperm and put a baby in that fat bitch, and his cheeks burned red to realize it was happening now.

"Hope you don't mind if we just... stay together like this a bit. I know you're dying to be fucked... but I'm just enjoying your body... it's not too oppressive, is it? Just having my fat thing stewin' in your guts."

"It feels... so big..."

"That's cuz you're so tight. Aw, you're shakin' all over. Don't be nervous, I got ya."

"I'm so embarassed..."

"Yeah? What's so embarassin'? Losin' your virginity with your butt? Givin' up your boyhole before gettin' your cock wet? Or just gettin' wrong-holed while dressed up like the sweetest, cutest little girly on the prairie? That ain't nothin' to be ashamed of, none of it... but you look so cute when ya blush that I'm gonna call you my little shithole slut anyways. Let's see the red in them cheeks, honey. Oh, you're tremblin' all over... if ya go weak in the knees, I got ya."

Her hands roam over his body as she kisses up and down his neck, her thick erection throbbing in his rear, making his stomach awkwardly cramp.

"Nnnh... you're so tight... you're so soft... your ass is so fat," she whispers into his ear, conspiratorially, and then nibbles on it. "It was made to be fucked," she says, with a voice now, directly into his ear, pressing her hips forward so that he feels an intense pressure in his stomach, which seems to outwardly bulge out slightly. "You know, whenever I say something like that, your dick starts drooling."

"Anh... ah..."

"Hey, wanna feel something weird?" she asks, but he feels something weird before he even responds - "it" jumps inside of him, making his bowels cramp... and sending a wave of pleasure and discomfort up his spine and back down cum pouch, yearning for release. Before he can even fully process it, she does it again - and his own cock twitches at the same time, and he wiggles his hips instinctively to dislodge the uppity intruder, but her hips follow him, a dirty dance with her cock in his dirty hole. "Hey, where are you going?" she asks, reaching under his "shirt" to pinch his nipple, "I'm not even fucking you yet."

She does it again, and again, until he's doubled over, her tail stuck in his backside, making him groan from a mix of intense ecstasy and discomfort, inadvertantly pushing his ass back at her as he does, so that her cock flicks up and down like a lever in his rounded-out hindquarters; that is, until she pulls him up by his chest and thrusts forward, flattening him out upright against the mirror, buried in his quivering hole, and his vision whites out.

For a second, he thinks that he's cum... but it's just more sticky, clear precum.

"Every time I twitch my cock insdie, you dribble more juice out..." she understates, while keeping him flat against the mirror with her fuckstick right up and twitching inside his shithole. "Do you want to be fucked?"

"Yes..." he says, the overwhelming sensation making it difficult to speak... "...fuck me... please..." he says, squirming against the mirror.

"You promise you'll be a good boy?"

"I am a good boy! Just fuck me!" he snaps, hoarsely.

"Whatever you say, princess. Don't say I never gave you anything."

"Nnnh... just shut up and fuck me!"

"You... got it... honey!" she says, punctuating it by thrusting in and out three times, and making his knees give out.

"Umngh... umg..." he moans as he inadvertantly bends over, giving his full ass to her as a target with a big fat bullseye painted on it. Every time she thrusts it all the way up into his rear, he feels it come out in his brain. She slaps her hips into his ass over and over again until finally, she grinds her hips against it and pulls up on his shoulder.

"If I took it out, what would you want me to do?"

"P-put it back in!"

"And if I didn't, would you beg?"

He nods his head.

"Don't worry, darlin'. It's not going anywhere until I knock one-and-a-half kids out up here where the sun don't shine," she says, giving him a little one-two hump that pokes into his front visibly, emphasizing her "point". "Now as much as I like seeing a boy with fat butt like you bending over, keep up straight so you can see how pretty you are."

"Nnnh... nh..." he grunts, feeling his ass tighten up around her.

"Oh yeah. Feel that twitching inside you? That's eight inches of my hot girlmeat, exploring your rectum the way it was meant to be explored. What do you think? Too much for your first time? Or just enough? Aw... you're drooling... guess little Miss Goldilocks thinks it's just right..."

Cyndey... Cyndey Goldilocks... that was his name... he wants her to ram her dick up his ass so bad - which is weird, because that's exactly what she's doing, over and over again.

"Hey... how do you feel about ass to mouth?" she says, running her long finger down his uvula. "Like it or love it? Boys like you seem to always love it. You can say you don't - I won't be mad. I'll just ask you to open your mouth after I'm done. But you definitely seem like the type who'll take it in the ass and the face, over and over, popping out of one and into the other... until I blow up in one, and forget which it was ten minutes later. There're boys who've never tasted my cum and boys who've never had to shit it out, pardon my French... and I couldn't tell you who was who. I gave it to em so much in both ends, it all sort of blurs together. Anyway, I'm babbling, when I should be crushing your prostate and churning your butter so you babble incoherently, right? You want me to wreck you, don't you? Give you such a good stuffing you start gobbling? Give you such a pounding you can't sit down? Give it to you in the wrong hole so much you mix up in and out? Up and down? Which way is it, baby? Am I going down your rabbit hole or up your shithole?"

"Up... my shithole..."

"Oh, you've got a dirty mouth. Not as dirty as it's gonna be when I forget which end of YOU is up, though. Probably dirtier than it would be if you weren't getting exactly what you wanted, huh? Come on, princess, show me your spoiled little o-face. You're a good boy who can cum from getting it anally, right?"

"Yesh..."

"Hear that naughty noise? I used so much lube that I'm churning it up... stuffing it up that wet, sloppy hole of yours... giving those hams of yours a nice glaze, right down the middle... you have such a nice figure... such nice, thick thighs and such a soft, fat ass...", she says, tracing her fingers down his waist, and hips and thighs... then back to his rear, which she cups as she thrusts. You've got a perfectly good cock, dear, but your best feature is definitely behind you... it'd be such a waste if... well, if I didn't ram my cock inside you. It's just got so much give... tell me, have you fantasized about someone taking you this way?"

"No..."

"Not once? Not once have you looked at yourself in the mirror and thought 'wow, someone should plow me like a field'? Never thought if you got on your hands and knees with your ass in the air that SOMEONE would fill your hole the way it needed to be filled?"

"Not really..."

"But you're going to now, right? You'll go out and buy a dildo?"

"Maybe..."

She sniffs his hair, absolutely cumdrunk. "You smell really nice, too... even though I'm blasting your ass, and you're sweating like a pig, you smell like flowers..."

"Don't say that..." he says, and then, his eyes go wide in realization.

"The big O... I see it in your eyes. You're about to cum so hard, aren't you? I haven't even touched this and you're about to have an earth-shaker, huh?"

He nods, expectant. He really is getting there, without touching himself. He can feel it building...

"Hey, don't cum until I say so, okay? I know with all that girldick in your ass you want to shoot off, badly, but hold it in, got it?"

"Oh, but I want to cum so bad..."

"I know hon, I know. You got what ya needed finally and you want to celebrate by painting the wall. Just hold out for me, baby. Can you do that?"

He whines, but nods, and she responds by picking up the pace, making him whine more. She gouges him and slops it all the way up his hershey highway, reaming him out every which way from behind, until he feels like he's ready to burst - in more ways than one.

"This must be torture for you..." she says, thumping into the bend in his rectum repeatedly, insistently, making him drool with desire. "Have you ever wanted to cum as bad as you do now?"

"No... I'll let you cum after... just please... let me cum..."

"I like hearin' you beg for it, hon, but just focus on bein' my dance partner for now. You'll get a chance to cream yourself silly when the time is right," she says... and then realizes that she's ready to blow herself. "You ready to catch what I wanna throw?

"I... I think so!"

"You think so? Say 'Charlene, cum in my fat ass! Cum in my belly! Fill me up and flush me out!"

"Charlene... cum up my ass... fill up my stomach... just make me cum!"

She runs her hand across his abdomen, reaching all the way around... then rubs his tummy in a circle. "Yeah... right in here," she says, tapping it twice softly, as he feels her cock twitch inside to emphasis her point. "You're blushin' again. Embarassed? You asked for it... now you gonna get it. I'm gonna fill up your belly with my hot goo like a stud..." she says, tapping it again, then rubbing it in a circle. "You're gonna feel my love butter percolatin' in your guts and are gonna love every drop of it. You ready to be creampied, hon? Is your belly ready to have its first dose of sex? Ready to get them bowels soggy? You ready to drink my milkshake the wrong way, Cydney?" she continues, pawing at his stomach and watching his face get redder and redder as his insides get closer and closer to being whitewashed and bloated. Then, she kisses up and down his neck, thrusting into his shitpit as she bangs him against the mirror... and then she sighs, hoarsely, into neck. "Oh yeah... honey, I've gotta blast," she says, with an urgency in her voice.

"Can I cum, then?"

"Do you want to?"

"...yeah..."

"You want to cum while I've got it all the way up in there?"

"Yeah..."

"You want to cum hard with a cock right up your shitbox?"

"Yes!" 

"Okay... I'll tell you when to cum... but first... I've got something for you," she explains, and he looks back at her, confused. "Watch my face... and get that stomach ready! I gotta fling nut so bad... right in your virgin ass! Right in your shitbox!"

He sees her face change, like she's trying to say something but can't, and she shudders... and then, he feels it; it's a sudden rush of warm liquid up his intestines. "Blast" was right - not only did it feel like he'd sat on a garden hose that somebody has just turned on, but he'd also lifted up when it hit, more surprise from the unfamiliar sensation than anything, and he squirmed to avoid catching too much of the hot, sticky goo, to no avail. He had never seen anyone orgasm in person before, and now he was watching someone as they came like a whale in his intestines... and all he could think about was cumming everywhere while being anally violated.

Not only does the increase in pressure push his button and make him want to cum even more, knowing that he's being cummed inside makes him want to cum on principle... and knowing that if he doesn't cum now, her hard dick isn't going to be stimulating him to spew his baby batter means that it's a now-or-never moment.

"Oh fuck... there it is... right up there..." she purrs, throbbing, twitching, and generally pumping her wicked girlslime in his fun tunnel while he waits with bated breath for her command.

"Can I cum?!"

"One... unh... second... just... hold... mmh..." she says, grunting through her sentence while obviously ejaculating wildly, which he feels as a building, diffuse pressure in his stomach. He has no idea what she's waiting for, and can't hold on much longer, but just as he's about to ask if he can cum, she kisses him, and he feels her tongue, and he feels her cum in his rectum, filling it up, and he feels her cock throbbing with the release he so desperately desires, and he feels her balls, pressed up against his thighs, pulsing as they empty.

Then... everything goes still. He still feels her gently throbbing, but she's not pulsing in twitching in a way that suggests the kind of pressurized cum-hosing she'd just been engaged in. She's breathing heavily and shuddering, but not thrusting or otherwise giving him the big D, meaning that even if he wanted to cum, he couldn't.

"Hey," she says, sleepily, brushing his face with the back of her hand, "who's a good little creampuff? You are. How's your stomach feel?"

"Full..."

"Mmhm... hey... I just poured my baby batter in your tummy. You didn't cum from getting creampied, did you?"

"No..." he whines.

"Good."

"Can I cum now?!"

"Such an impatient boy," she says, cupping his swollen balls, "although... these have some heft to them, so I can see why... you have to blast as much as I just did. Trust me, I know how you feel... it felt so good to finally let it all out inside of you... I feel like if I squeeze one of these little funbags just a bit, you'll shoot off."

"Hnyh..."

"What a state you're in... you know, I came, but I'm still pretty hard. I could... give you what you need..."

"Please... please... just fuck my ass..."

"'Just fuck my ass' he says. Is that all I am to you? A nice rack with a big dick? I have feelings, you know. And a softening, if still pretty stiff, dick..." He starts to press his ass back at her, moaning, trying to fuck himself on her shaft, but he can't get the angle right...

"Oh, you're going to fuck yourself on it, is that it? Hold still. Now I've just got to pull out very carefully or I'll trigger it and you'll fling your goo all over the place."

"Now tighten up once it pulls out, so you don't make a mess. Annndd... there. Just a little wet wipe on your tip and... all good. Ta-da! No clean-up!"

The ground falls out beneath him. His butt was absolutely full of cum, sure... but so were his balls! What the fuck?! His outrage only lasts a second, however, before a more pressing need is pushed to the forefront.

"It's coming out..." he says... buckling at the knees and trying to clench his recently-fucked hole.

"Ah-ah-ah... you'll get it everywhere. Either do it in the toilet, or wait."

"But... I... I didn't... I didn't cum."

"Don't worry, I came enough all up in your guts for both of us," she says, rubbing his now-slightly flabby tummy, making him seriously consider finishing the conversation through a bathroom door.

"What... the fuck..."

"Such a potty mouth... relax, hon, I didn't do it to be mean. I want ya to enjoy this, after all."

"So... you'll make me cum?"

"Eventually. It was a mean little trick I played on you, I know. But trust me, I'll make it worth your while. In a way, I already have, haven't I?"

"Yeah, but... I just... want to cum..."

"You ever hear of orgasm denial? Well, crossdressin's your fetish, and that's mine. I like to give it to a boy from behind until he's fit to bursting and then... well, I suppose you know, now. I like hearing boys say they want to cum with their hole, and only with their hole - and there's no better way to get them sayin' it then to tell 'em they can't have it. If I tried to stroke you off right now you'd hiss like a cat. While cumming, obviously, but still. You've got an itch right now that only I can scratch... anally. Right?"

"Yeah..."

"Sometimes I wrap a rubber band around it, or just squeeze it real hard at the base - but not toucing it at all has got it's own charm. If I make you cum, eventually, will you forgive me?"

"Yes! I will!"

"Good... then I'll fuck you every which way before then. We're gonna fuck on every floor, counter-top and table in this house, and you're not gonna pop till we're done. I'm gonna fill you with so many rounds it's gonna be like  
a drive-by enema. Okay?"

"Anything..."

"If you get me ready, I'll blast your ass and face hole as much as you want. But first, I think I need to teach your mouth what I just taught the other end. So open wide."

And so, sitting on the floor, he opens wide... knowing that it wasn't the beginning of the end, but the end of the beginning... and that might by the time the night was over, she was going to have swapped between his face and ass a half a hundred times - but it didn't matter, as long as, just one of those times, she stayed in his ass long enough to give him what he wanted... no matter how much semen pudding he had to swallow orally and anally...


End file.
